We Asked Chicagoans For Their Favorite Movies That Feature The City - The Answers Were Pure Gold

We asked our Facebook page of 60k Chicago lovers one simple question: What’s are the best movies that features our beloved city? The answers poured in, and there was one clear winner! Here are the movies Chicagoans love most! ## The Blues Brothers (1980)  Hands down the winner, every single time this question comes up. This is *our* movie. From the old Maxwell Street market chaos to that insane chase tearing through Lower Wacker and piling up cars in Daley Plaza, it’s the ultimate love letter to late-’70s Chicago. Ray Charles, Aretha, James Brown—all showing up while Jake and Elwood dodge Nazis and wreck everything in sight. Locals still quote it daily and grin every time they drive past a spot that got immortalized in the madness. ## Ferris Bueller’s Day Off (1986)  If any movie makes you want to call in sick and spend the day tearing around the city, it’s this one. Wrigley Field, the Art Institute, the (old) Sears Tower, lip-syncing on a parade float down Dearborn—Ferris gave the world the ultimate Chicago tourist checklist disguised as the perfect hooky day. Locals who grew up here say it’s the one that feels most like home, and yeah, it’s a big reason plenty of us moved here in the first place. ## Cooley High (1975)  The Black *American Graffiti*. Shot around the real Cabrini-Green and the old Cooley Vocational High School, it’s pure early-’60s nostalgia—hanging out, cruising, getting into harmless (and not-so-harmless) trouble. A whole generation of Chicago kids grew up seeing their own lives reflected back, and it still hits hard for anyone from the North Side who remembers that era. ## The Untouchables (1987)  That Union Station staircase shootout alone secures its spot. Brian De Palma turned LaSalle Street into Prohibition Chicago, David Mamet wrote the script, and Sean Connery owned every scene. Locals still walk those stairs and hear the baby carriage bouncing in their heads. Pure drama, pure style, pure Chicago history. ## Hoop Dreams (1994)  Not a scripted movie, but maybe the most honest Chicago story ever put on film. Following two kids from the inner city chasing basketball dreams, it shows the real grind, the hope, the heartbreak. Locals call it required viewing if you want to understand what growing up here can feel like when hoops are your only ticket out. ## High Fidelity (2000)  John Cusack brooding over top-five lists in a Wicker Park record store that felt ripped straight from real life (it basically was). Green Mill, Double Door, Lounge Ax, Rainbo—every spot nailed the neighborhood at its boho peak. Anyone who ever worked retail or nursed a breakup over vinyl knows this one by heart. ## Judas and the Black Messiah (2021)  Daniel Kaluuya as Fred Hampton, LaKeith Stanfield as the informant—it’s heavy, powerful, and unflinching about a crucial piece of Chicago history. Shot here, rooted here, and still sparking conversations every time it comes up. Locals say it’s essential viewing for understanding the city’s past and present. ## Thief (1981) Michael Mann’s neon-drenched masterpiece. James Caan cracking safes under rainy streetlights, diners glowing at 3 a.m.—it’s nocturnal Chicago at its most atmospheric. Locals who love the gritty side swear this one captures the city’s soul better than almost anything else. ## Medium Cool (1969)  Shot during the chaos of the 1968 Democratic National Convention, it blends fiction and real protests so seamlessly you can’t tell where one ends and the other begins. Robert Forster as a news cameraman caught in the middle—it’s raw, urgent, and still feels like a time capsule of Chicago in upheaval. ## Ordinary People (1980)  Mostly shot up in Lake Forest, this one’s quiet, devastating family drama after a tragedy. Timothy Hutton and Mary Tyler Moore tearing each other apart in beautiful North Shore houses. Locals recognize those tree-lined streets instantly and still argue over who was more heartbreaking. ## The Fugitive (1993)  Harrison Ford on the run, diving off dams, blending into the St. Patrick’s Day parade—it’s nonstop, and the Chicago chase scenes are the climax. Locals flip every time they spot the Hilton or drive past parade routes and hear “YOU SWITCHED THE SAMPLES” in their heads. ## Mean Girls (2004)  Yes, it’s North Shore high school drama, inspired by New Trier and Evanston. Tina Fey wrote it while doing Second City gigs, and it’s sharp, quotable, and secretly very Chicago under the pink glitter. ## Home Alone (1990)  That Winnetka mansion, O’Hare chaos, and little Kevin defending his suburban castle—it’s Christmas tradition for half the city. Locals who grew up in the burbs swear the house parties and pizza obsession feel ripped from real life. ## Candyman (1992) Shot inside the actual Cabrini-Green projects, it’s terrifying and tragically real. The urban legend, the hook, the commentary—it’s horror that still resonates because it was filmed where the stories came from. ## The Breakfast Club (1985) Detention in a suburban library (shot at closed-down Maine North High), five archetypes becoming real people. It’s John Hughes at his most universal, and locals still quote it constantly. ## Road to Perdition (2002) Tom Hanks as a mob hitman, Depression-era looks all over downtown and the University Club. Rain-soaked streets and moral gloom—Chicago has never looked more beautifully moody. ## The Man With The Golden Arm (1955) Frank Sinatra fighting heroin addiction in a North Side walk-up. Groundbreaking for its time and still a gut-punch performance. Locals respect it as one of the earliest films to tackle the city’s darker realities head-on. ## A League of Their Own (1992) Wrigley Field tryouts for the real-life Rockford Peaches. It’s not Cubs or Sox, but it’s still the best baseball movie Chicago ever gave the world. ## Wayne's World (1992) Technically Aurora, but Stan Mikita’s Donuts and the Blackhawks love make it undeniably ours. Party on. ## Widows (2018) Viola Davis pulling off a heist amid dirty Chicago politics. That single-take drive from the South Side to the mansions says everything about the city’s divides in one unbroken shot. ## The Sting (1973) Paul Newman and Robert Redford conning their way through Depression Chicago. Union Station cameos, ragtime revival—it swept the Oscars and still feels like classic Chicago hustle. ## Henry: Portrait of a Serial Killer (1986) Dark, disturbing, and shot in the working-class corners most movies ignore. Not tourist-board friendly, but unflinchingly real. ## Southside With You (2016) Barack and Michelle’s first date, wandering the South Side, hitting the Art Institute. It’s modern Chicago legend turned sweet, sunny romance. ## Drinking Buddies (2013) Revolution Brewing taproom, Empty Bottle, Half Acre shirts—pure Chicago craft-beer scene. Olivia Wilde and Jake Johnson mumble their way through messy relationships that feel like every weekend here. ## Running Scared (1986) Billy Crystal and Gregory Hines buddy-copping all over the city, including that wild El track car chase. Underrated gem that feels right at home on our streets. ## Adventures in Babysitting (1987) Elizabeth Shue dragging suburban kids into downtown chaos for one crazy night. Blues clubs, skyscraper climbs, and that classic fear of “the city” from the burbs—it’s hilarious and still nails the vibe. ## My Best Friend’s Wedding (1997) Julia Roberts racing around O’Hare, the El, Fourth Presbyterian Church, causing rom-com havoc. Chicago looks gorgeous, and locals still tear up at the ending. These are the ones that keep coming up when Chicagoans talk movies. They’re woven into the city’s fabric—spots you drive past, bars you drink in, history you live with. Next time one pops up on streaming, throw it on. You’ll spot home everywhere.